(3aR,5S,6E,10Z,11aR)-5-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one

Details

• Internal ID: 2709630c-41e2-419f-b956-da147e05e3ab
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (3aR,5S,6E,10Z,11aR)-5-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one
• SMILES (Canonical): CC1=CCCC(=CC2C(CC1O)C(=C)C(=O)O2)CO
• SMILES (Isomeric): C/C/1=C\CC/C(=C/[C@@H]2[C@H](C[C@@H]1O)C(=C)C(=O)O2)/CO
• InChI: InChI=1S/C15H20O4/c1-9-4-3-5-11(8-16)6-14-12(7-13(9)17)10(2)15(18)19-14/h4,6,12-14,16-17H,2-3,5,7-8H2,1H3/b9-4+,11-6-/t12-,13+,14-/m1/s1
• InChI Key: QKQGXZIVYKJKBQ-SEAOSHTHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.13615911 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): 1.49
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9820	98.20%
Caco-2	+	0.6008	60.08%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7043	70.43%
OATP2B1 inhibitior	-	0.8588	85.88%
OATP1B1 inhibitior	+	0.9059	90.59%
OATP1B3 inhibitior	+	0.9594	95.94%
MATE1 inhibitior	-	0.9212	92.12%
OCT2 inhibitior	-	0.5863	58.63%
BSEP inhibitior	-	0.9400	94.00%
P-glycoprotein inhibitior	-	0.8904	89.04%
P-glycoprotein substrate	-	0.8590	85.90%
CYP3A4 substrate	+	0.5416	54.16%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8359	83.59%
CYP3A4 inhibition	-	0.7729	77.29%
CYP2C9 inhibition	-	0.9221	92.21%
CYP2C19 inhibition	-	0.8596	85.96%
CYP2D6 inhibition	-	0.9063	90.63%
CYP1A2 inhibition	-	0.6816	68.16%
CYP2C8 inhibition	-	0.7616	76.16%
CYP inhibitory promiscuity	-	0.8996	89.96%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6909	69.09%
Eye corrosion	-	0.9822	98.22%
Eye irritation	-	0.8463	84.63%
Skin irritation	-	0.6385	63.85%
Skin corrosion	-	0.9344	93.44%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7802	78.02%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	+	0.5875	58.75%
skin sensitisation	-	0.8368	83.68%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.7277	72.77%
Acute Oral Toxicity (c)	III	0.5693	56.93%
Estrogen receptor binding	-	0.6370	63.70%
Androgen receptor binding	-	0.6791	67.91%
Thyroid receptor binding	-	0.5903	59.03%
Glucocorticoid receptor binding	+	0.7969	79.69%
Aromatase binding	-	0.7351	73.51%
PPAR gamma	-	0.5961	59.61%
Honey bee toxicity	-	0.8910	89.10%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9387	93.87%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.72%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.21%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.64%	97.09%
CHEMBL2581	P07339	Cathepsin D	88.71%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.56%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.42%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.56%	100.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.35%	95.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.64%	94.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.56%	93.03%

Plants that contains it

• Tetraneuris turneri

Cross-Links

• PubChem: 162955560
• LOTUS: LTS0189645
• wikiData: Q105223267